14 Legendary Trades and Free-Agent Signings That Almost Happened

What if Tim Duncan had gone to the Magic? Or Alex Rodriguez been traded to the Red Sox? We look at the earth shaking moves that almost happened.

Tim Duncan Magic Jersey Complex Photoshop
USA Today Sports

Tim Duncan Magic Jersey Complex Photoshop

Tim Duncan Magic Jersey Complex Photoshop

You miss 100 percent of the shots you don’t take. Michael Scott of The Office famously said that, quoting Wayne Gretzky.

And a lot of teams on this list missed a lot of big shots in both trades and free agency. Whether it be general managers having last-second changes of heart, a union meddling, or some other reason, so many trades with legendary potential fell through over the years just as they were about to change history.

It’s always fun to think of what could have been, especially if your team hasn’t had much to cheer about over the last couple of decades. Had some of the trades on this list happened, they would have altered the history of leagues and franchises—turning losers into winners and winners into losers. Heck, the Montreal Expos might still be in existence if one of the trades on this list went down.

So let’s take a look at 14 trades and free agent signings that almost happened. You probably didn’t even know that most of these even existed. And a trigger warning for Raiders fans: They made the list three times. Narrowly missing out on three Hall of Fame quarterbacks.

1983: John Elway is traded to the Raiders.

John Elway Broncos Raiders Oakland 2016

1989: Dan Marino is traded to the Raiders.

Dan Marino Miami Dolphins Oakland 1998 Getty

1992: Barry Bonds is traded to the Braves.

Barry Bonds Pirates 1991 Getty

1992: Charles Barkley is traded to the Lakers.

Charles Barkley analyzes the NBA.

The Sixers and Lakers actually agreed to a deal in 1992 that would send Charles Barkley to Los Angeles in exchange for James Worthy and Elden Campbell. The deal was so close to happening that Barkley went out and had a couple of drinks to celebrate. Per Barkley, from a 2015 SI interview:

“It was going crazy for two weeks so I knew it would come down to Portland, [the] Lakers or Phoenix. So I get a call from my agent one morning and he said, “Philly has traded you to the Lakers.” So I went to lunch and started drinking. I’m f---ing so excited that I am going to the Lakers. Three hours later I get a f---ing phone call from my agent saying that the Sixers backed out of the deal. I said, “Oh, s--t, I’m feeling pretty good right now.” So I went out and played that night.”

It’s unclear when exactly in 1992 this happened, but Barkley said he played well that night. He was eventually traded to the Suns that off-season, where he took the team to the NBA Finals in his first year in Phoenix.

This trade was very close to becoming reality. Back in March 2016, we outlined how one of the most monumental NBA trades of the 90s almost went down

Kemp remembers how close the trade was to happening. “[Sonics owner Bob] Ackerley called me and told me they weren’t going to make the trade,” Kemp said. “He was telling me people were calling the local radio stations saying they were going to burn down the stadium if I was traded.” Just prior to the 1994 draft, the Sonics told the Bulls the deal was off.

Then in 1997, the Bulls agreed to send Pippen to the Raptors for a rookie draft pick named Tracy McGrady—but it was rejected by Michael Jordan. McGrady later expressed relief that Jordan nixed the trade, saying “I know I wasn’t qualified to fill the shoes of Scottie Pippen at the moment, I’ll tell you that.”

The Bulls’ dynasty could have ended much differently had either of these trades gone through. Speaking of non-trades that preserved dynasties...

1995: Mariano Rivera is traded to the Tigers.

Mariano Rivera Yankees Tigers 2013 Getty

Rivera was very nearly dealt to Detroit in 1995 for another future Yankee: David Wells.

Then-Yankees GM Gene Michael was actively considering trading the future Yankees closer—who was a starting pitcher in Triple-A at the time—to the Tigers in 1995, and Detroit said they would want Rivera in a prospective trade for Wells. The Yankees were actively contending for their first postseason spot in 14 years, and were looking for help in their rotation.

A trade for Wells seemed to make sense. Then, one perfectly timed scouting report prompted Michael to take Rivera off the block. From the New York Daily News:

"I never said yes," Michael said with a chuckle. "And right about that time, Mariano's velocity in the minors jumped to 95-96. I didn't believe it when I saw our report, but I checked it out with scouts from other teams who were there, and it was true. At that point there was no way I was trading him."

Rivera’s velocity had previously only been in the low 90s. Had he not had this velocity uptick, “Enter Sandman” might have been the most popular song in Detroit for almost 20 years.

1996: Reggie Miller signs with the Knicks.

Spike Lee Reggie Miller Alex Rodriguez 2009 Getty

If you’d ask any Knicks fan to name their most hated NBA player of all time, there’s a good chance they’d tell you it’s Miller. I mean, we’re talking about the guy who dropped eight points in nine seconds on them and made his infamous choking gesture at Knicks superfan Spike Lee.

But had he signed with the team in 1996—which was reportedly a strong consideration—he may very well have his name hanging from the rafters at Madison Square Garden today.

Miller considered teaming up with Patrick Ewing in New York to form a superteam to rival the Bulls. These plans ultimately fell through when the Knicks opted to sign Allan Houston instead. Here’s an excerpt from a 1998 New York Daily News article detailing how that all went down:

The Knicks finally signed Houston, while Miller was in Atlanta for the 1996 Olympics. The Indiana player got the news at the U.S. team's hotel, and went whining to U.S. teammate Grant Hill of the Pistons. "Your guy just ruined my plans," Miller told Hill. Nobody really knew what Miller's plans might have been, including Houston. "I didn't care," Houston said yesterday. "I did what was the best situation for me.

Houston was 25 at the time while Miller was 31, so Houston was seen as having a bigger upside. The Knicks’ shootin guard did indeed make a major impact in New York—before knee injuries prematurely derailed his career.

Still though, the thought of Miller in a Knicks uniform is a strange one. It would have been curious to see whether an Ewing-Miller Knicks squad could have knocked the Bulls off in the playoffs.

2000: Tim Duncan signs with the Magic.

Gregg Popovich Tim Duncan 2015

2000: Albert Pujols is traded to the Expos.

Albert Pujols Cardinals Expos 2001

2004: Alex Rodriguez is traded to the Red Sox.

Alex Rodriguez Yankees 2005 Getty

2004: Terrell Owens is traded to the Ravens.

Terrell Owens Ravens Eagles 2004 Getty

This was another trade that was agreed to, but never officially went through. The Ravens were to send a second-round pick to the 49ers for T.O., who refused to show up for a physical in Baltimore. Owens was ultimately traded to the Eagles, the team he wanted to play for. Since this trade never went through, the Ravens settled with the 49ers and received a fifth-round pick as compensation for the trade that never was.

That season, Owens again drew the ire of Baltimore fans when he impersonated Ray Lewis’ classic dance after scoring a touchdown against the Ravens:

2006: Drew Brees signs with the Dolphins.

Drew Brees Saints Dolphins 2013 Superdome Getty

2007: Aaron Rodgers is traded to the Raiders for Randy Moss.

Aaron Rodgers Packeres Raiders 2016

This one may have been more of a rumor than anything else. But it was apparently serious enough that Deadspin did an article on the matter in 2007 titled “We Repeat: Please Let the Moss Trade Happen,” in which it said that a Moss-Rodgers trade was imminent, citing a Boston Herald report. At this time, Rodgers was Brett Favre’s backup, and the Packers lacked an elite receiver.

According to former Packers exec Andrew Brandt, Moss was indeed almost a Packer. From a 2012 ESPN article:

In 2007, the Raiders made Randy Moss available. We were interested provided we could agree on trade terms and compensation. The Patriots were interested, too.

Moss demanded a one-year deal so he could hit the market after the season and recoup some lost value, but we insisted on a two-year deal. We did not want to be a temporary stop for him before he made another big contract elsewhere. When New England relented on the one-year term, Moss was a Patriot.

The Pats eventually acquired Moss for a fourth-round pick, so it seems unlikely that it would have required a former first-rounder like Rodgers to finish the deal. Green Bay made a huge mistake by not giving in to Moss’ demands; the Packers made it all the way to the NFC Championship game in 2007 without Moss. Imagine what they could have done with Moss.

Kobe Bryant to the Wizards/Clippers/Bulls.

Kobe Bryant after his final NBA game.

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